#935 Multifamily in Transition: Strategies for Today's Market with Gary Lipsky

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp

Investing, Education, Business

4.8 • 679 Ratings

🗓️ 18 August 2025

⏱️ 30 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Gary Lipsky is the president of Break of Day Capital, an investment firm that specializes in multi-family real estate in Arizona. Gary brings a 20+ year track record in the real estate space and has completed more than $300M of transactions over his career. Gary is also the host of the Real Estate Investor Podcast, where he interviews industry experts to provide broad range education to investors. He is also the best-selling author of Best in Class, founder of the Asset Management Summit, and a guest speaker featured at many prominent conferences.

Connect with Gary: breakofdaycapital.com

Highlights:

02:55 – How Gary's entrepreneurial roots and first house hack in Los Angeles planted the seed for a multifamily career.
04:10 – Current challenges in Arizona
06:00 – Why today's market offers opportunity
09:50 – Outsourcing property management
12:45 – Experimenting with AI for investor communications, research, marketing
19:00 – The capital raising challenge
21:10 – Advice to LPs: focus on the operator's track record and discipline

Quote: "If a deal sounds too good to be true, it probably is. Don't chase IRR or bonus depreciation—chase a good operator, and everything else will work out."

Recommended Resources:

Accredited Investors, you're invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!
If you're a high net worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.
Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.
Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.

Transcript

Click on a timestamp to play from that location

0:00.0	You've been searching for the best way to generate passive income in your life and heard that real estate is a great way to do it.
0:09.4	But you're tired of all the so-called gurus who are all talk and no substance.
0:15.3	Get ready to celebrate because Kevin Buck has spent 14 years successfully making it happen. This is the Real Estate
0:22.8	Investing for Cash Flow podcast. Now, here's Kevin Bup. Hey guys, Kevin Bup here, and I want to
0:31.9	welcome me to another episode of the Real Estate Investing for Cashflow podcast.
0:35.4	We're missions that help you build and maintain massive amounts of cash flow through income
0:39.6	producing real estate investments.
0:41.5	Our guest for this week's show is a real estate investment expert Gary Lipski.
0:44.9	Gary is the president of Break of Day Capital, an investment firm that specializes in
0:49.3	multifamily real estate in Arizona.
0:51.5	Now Gary brings a 20 plus year track record into the real estate space
0:54.6	and has completed more than 300 million of transaction over his career. Gary's also the host of
0:59.2	the real estate investor podcast where he interviews industry experts to provide a broad range of
1:03.6	education to various investors. I was this on the show a few weeks back as well. In addition to that,
1:09.8	Gary's also the best-selling author of Best in Class.
1:12.7	He's the founder of the Asset Management Summit
1:14.4	and a guest speaker featured at many prominent conferences.
1:17.1	And so, guys, without further ado, I like to welcome Gary Lipski to the show.
1:20.6	My friend, how are you today?
1:22.5	Good. Thanks for having, Kevin.
1:23.6	Yeah, excited to have you here.
1:24.8	I know I was on your show a few weeks back, maybe a few months now. I lose track of time. They all kind of days blend together, right? But I know excited to have you, you know, flip the tables here today and have you on our show. So why don't we, let's just back it up a little bit. Let's give you the opportunity, Gary, for those that aren't familiar with you that don't know you, don't know your story, maybe back it up and just tell something more about yourself personally and how you found your way into real estate.
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Kevin Bupp, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Kevin Bupp and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.